Top Vacation Rentals in Cheshire, MA for Unforgettable Stays

Located in New Ashford, 19 miles from Cranwell Spa & Golf Club, The Springs Motel provides accommodations with a seasonal outdoor swimming pool, free private parking, a garden and a terrace. Each room at the 4-star hotel has mountain views, and guests can enjoy access to a bar and to water sports facilities. The property has a concierge service and free WiFi. Complete with a private bathroom equipped with a shower and free toiletries, all guest rooms at the hotel have a flat-screen TV and air conditioning, and some rooms here will provide you with a balcony. The rooms will provide guests with a fridge. The Springs Motel has a grill. Tanglewood Musical Center is 19 miles from the accommodation, while Tanglewood is 19 miles away. Albany International Airport is 39 miles from the property.

- "Loved our stay, definitely would return" - "Memories were made that will last a lifetime and we definitely want to come back someday! Thank you!" - "Will definitely stay here again if we’re in the area." - "The loveliest motel I've ever stayed at" - "Perfect location!" - "Nice, retro place to stay. Close enough to Williamstown" - "Convenient." - "Cute, elevated motel" - "Loved it!" - "A lovely place but absence of management during the day."

Bed & breakfast in Cheshire with free breakfast
Coffee/tea in a common area, a library, and express check-in are available at this bed & breakfast. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, express check-out, wedding services, and a garden are onsite.
Housekeeping is not available.
Harbour House Inn offers 6 accommodations with bathrobes and hair dryers. Each accommodation is individually furnished and decorated. Satellite television is provided.

Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include complimentary toiletries and ceiling fans.

- "Decorations were beautiful, room and bed were so comfortable, hostess and food were wonderful. Brandi was thoughtful in every way possible. Can't go wrong choosing this place over a chain. Love it!" - "Lovely space and welcoming host." - "We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "

Offering a tennis court, Mountain getaway in the Berkshires - walk to trails & town! offers accommodations in Adams. This vacation home features air-conditioned accommodations with a patio. There's an outdoor fireplace and guests can use free Wifi and free private parking. Featuring a terrace and mountain views, the spacious vacation home includes 4 bedrooms, a living room, cable flat-screen TV, an equipped kitchen, and 2 bathrooms with a bath and a shower. Towels and bed linen are available in the vacation home. There's also a seating area and a fireplace. Guests at the vacation home will be able to enjoy activities in and around Adams, like skiing, cycling, and fishing. Outdoor play equipment is also available at Mountain getaway in the Berkshires - walk to trails & town!, while guests can also relax in the garden. Tanglewood is 23 miles from the accommodation, while Cranwell Spa & Golf Club is 24 miles from the property. The nearest airport is Albany International Airport, 48 miles from Mountain getaway in the Berkshires - walk to trails & town!.

Balcony/Terrace • View • Internet • Parking • Air Conditioner • Child Friendly • Ocean View • Other • Kitchen • Pet Friendly

While you're here, you can enjoy all the comforts of home and more, including a refrigerator and free WiFi, as well as an LCD TV and a coffee/tea maker. Other amenities include towels, slippers, a desk, and housekeeping.

- "The Revival House was charming and quiet. It had everything we needed for our short stay. It's only a 6 minute drive to the Bellows Pipe Trail/Mount Greylock, which was a huge plus for us. Wishing all the best for this newly opened hotel!" - "Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and " - "The inside is perfect. The neighborhood is unkept. A week of landscapers would make first impressions better. That being said the cover of the book is worn, the real treasure is the inside. I want this new hotel to succeed. It’s has an indescribable quality that makes this a must stay. "

The Trail in Adams - Berkshires' Art Hotel provides a hot tub and air-conditioned accommodations in Adams, 23 miles from Cranwell Spa & Golf Club. Among the various facilities are a garden, a terrace, and a shared lounge. The accommodation offers a sauna, free Wifi throughout the property, and family rooms. The bed and breakfast offers a flat-screen TV and a private bathroom with slippers, a hair dryer, and shower. At the bed and breakfast, all units are allergy-free. At the bed and breakfast, units come with bed linen and towels. The Trail in Adams - Berkshires' Art Hotel offers a vegetarian or gluten-free breakfast. For guests with children, the accommodation features an indoor play area. Skiing, cycling, and hiking are possible within the area, and The Trail in Adams - Berkshires' Art Hotel offers ski storage space. Tanglewood Musical Center is 23 miles from the bed and breakfast, while Tanglewood is 23 miles from the property. Albany International Airport is 48 miles away.

- "Charming bed and breakfast with friendly, accommodating owners." - "Excellent" - "Awesome vibes at The Trail in Adams!" - "Pleasant stay in updated small arts-oriented hotel in an up and coming small city." - "Will Return Again" - "Nice place to stay" - "I can’t wait to come back!" - "Pleasantly surprised!" - "Form over function"

With close access to the Ashuwillticook rail trail and a short drive to convenient shopping and restaurants, this is a perfect location for your Berkshire getaway. Relax on the private back porch, or in the large bath tub. Cook meals in the full kitchen, or do some writing at the desk with views of the pond. Sleep in late in the king sized bed, and then enjoy what the Berkshires has to offer! 5 minute drive to Lakeview Orchards, 20-25 minutes from Lenox, Tanglewood, and Kripalu. 30 minutes to Mass MoCA and the peak of Mount Greylock (less to the start of the trails, if you want to hike it yourself!). 5 minute drive to Jiminy Peak, 45 to Berkshire East and Butternut ski resorts. 20 minutes to Notchview for cross country skiing.

This is a unique old house, and you will find nautical books and artifacts, as well as trinkets from around the world. Please note that there is no TV. The spiral staircase is one of my favorite features of the house, but it is narrow and steep, so please take care. If there will be more than two guests, and you require complete privacy from those staying on the couch downstairs, you might want to rethink, as the house is small and the bedroom upstairs is a loft. The bedroom upstairs has low ceilings - but with a comfy king sized bed, there's no need to stand up for too long, anyhow! In addition to the full bathroom downstairs, there is a half bath on the second floor, so one does not have to navigate the small staircase after bed time. The second bed, a pull out couch downstairs, is queen sized and very comfortable.

- "The cottage was clean and as described. The street was very quiet." - "This property is located near some great hiking, biking and swimming and is a great place to stay. If we had a question it was responded to in a very timely and professional manner. The owner made us feel more than welcome and went out of their way to make our stay exceptional. I would certainly stay here again!" - "We had a very enjoyable stay. The owner provided some basics such as coffee, tea and spices. The first level consists of the kitchen, living/dining room combo. There is a narrow spiral staircase to the bedroom which has access to a toilet and sink. We didn't stay up there as the pitched roof is too close to the bed and it was cold. The bathroom has a nice washer/dryer however the baseboard heater doesn't provide enough heat so it felt frigid. There is spa tub suitable for soaking but if you less agile you may have trouble getting into the tub. The living room couch opens to a double bed with linens in the storage part of the couch. There was good heat on the first level and the hot water heats up quickly. The house is situated close to Target and the Regal Berkshire movie theatre. It is 15-20 minutes to area attractions such as Edith Wharton's house, Ventford Mansion, Norman Rockwell Museum and Clark Art Institute, etc. We would stay here again."

Situated in Adams, 37 km from Tanglewood and 37 km from Cranwell Spa & Golf Club, Charming Adams Home Near Dtwn, Trails and More! offers air conditioning. This holiday home is 45 km from Norman Rockwell Museum and 19 km from The Clark Art Institute. With free WiFi, this 1-bedroom holiday home features a cable flat-screen TV and a kitchen with an oven and microwave. Towels and bed linen are offered in the holiday home. Tanglewood Musical Center is 37 km from the holiday home, while Bennington Battle Monument is 42 km from the property. The nearest airport is Albany International Airport, 77 km from Charming Adams Home Near Dtwn, Trails and More!.

Child Friendly • Internet • Wheelchair Accessible • Parking

Bed & breakfast with free parking, steps from Adams Theater
This smoke-free bed & breakfast features coffee/tea in a common area, a microwave in a common area, and a refrigerator in a common area. Free WiFi in public areas and free self parking are also provided. Other amenities include an arcade/game room, express check-in, and a garden.
The Trail in Adams - Berkshires’ Art Hotel offers 9 air-conditioned accommodations with slippers and hair dryers. These individually decorated and furnished accommodations include desks. Beds feature premium bedding. Televisions come with digital channels, pay movies, and Netflix. Guests can surf the web using the complimentary wireless Internet access. A nightly turndown service is provided and housekeeping is offered daily.
The recreational activities listed below are available either on site or nearby; fees may apply.

- "Went to Solid Sound music fest in North Adams and needed a place to stay. The Trail was available and we were pleasantly surprised!" - "nice comfortable and funky!" - "We loved this place, it was fun, quirky and cute. It felt like being at home, honestly. I have an injury and the staff was able to accommodate an earlier check-in without any issue. The staff was very kind and responsive. My fiancé loved the shower sauna! Awesome place to stay!"

Lakeside Berkshires Home Near Hiking and Skiing! is located in Lanesborough, just 12 miles from Tanglewood Musical Center and 13 miles from Tanglewood. This vacation home features accommodations with a balcony. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 12 miles away. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are available in the vacation home. The property has an outdoor dining area. Norman Rockwell Museum is 18 miles from Lakeside Berkshires Home Near Hiking and Skiing!. Albany International Airport is 43 miles from the property.

Guest Services • Accessibility • Child Friendly • Spa • Internet • Parking • Security/Safety • Other

Motel in New Ashford with free parking
This motel features a seasonal outdoor pool, a garden, and charcoal grills. Free WiFi in public areas and free self parking are also provided. Other amenities include a picnic area and a banquet hall.
Housekeeping is available on request.
The Springs Motel offers 20 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and complimentary toiletries. Each accommodation is individually furnished and decorated. Smart televisions are featured in guestrooms.

Bathrooms include shower/tub combinations. This New Ashford motel provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). Housekeeping is provided on request.

- "Great motel! Clean, well-decorated, decent-sized rooms and a lovely grassy courtyard with comfy furniture, picnic tables, umbrellas, and fire pits. Although right off the highway, the road noise was minimal and it was a very relaxing place to crash for a night. " - "We really enjoyed the wonderfully updated Atomic ranch style. It had all the 50’s charm With a nicely updated, modern feel. Rooms were well appointed, clean and great to stay in. Mattress and pillows were comfy and we thoroughly enjoyed our stay."

This Lanesboro, Massachusetts motel is located less than 1 mile from Pontoosuc Lake and features free Wi-Fi access and cable TV in every room. Balance Rock State Park is 2 miles away. The Weathervane Motel Lanesboro features rooms with a microwave and a refrigerator. They also offer coffee making facilities and an private bathroom with a hairdryer. Guests can relax in air conditioned comfort at the Lanesboro Weathervane Motel. A garden and vending machines with drinks are also available. The Berkshire Museum is 10 minutes’ drive from the motel. The Bousquet Ski Area is 7.8 mi away, while the Jimmy Peak Ski Area is 8.2 mi away.

Air Conditioner • Child Friendly • Guest Services • Internet • Fireplace/Heating • Other • View • Skiing • Parking

Just bring your clothes and food! Everything else is here. Everything to cook with clean, shower, extra linens and blankets. Nice front and back porches.

Plenty of parking. Centrally located in the beautiful Berkshires, a short drive to anything. The stairs are very quirky and not for the faint at heart. You'll love them or hate them! See picture.

***NOTE: We are family-friendly! We make an extra effort to ensure that children and pets feel welcome and are comfortable. No breed or size limits for dogs!

180-year-old home with plenty of modern updates to make anyone feel at home.

2 bedrooms , one with a king bed and the other with a trundle with 2 twin beds. There is a Queen air mattress, able to be set up in any room guests choose. Pack and Play with sheets and blankets is also always available and can be used in any room. Extra sheets, blankets, and pillows are always available.

There is other equipment for traveling babies and toddlers, such as an infant swing, boppy, Bumbo seat, wagon, and toys. A stroller can be provided with advance notice.

The modern bathroom features a large walk-in shower and a hair dryer for convenience.

WiFi and smart TVs make your downtime relaxing. Alexa in the kitchen can be moved to any room you choose.

Modern washer and dryer is available for use at any time at no charge.

Experience what the Berkshires has to offer in this centrally located home in the friendly and safe town of Dalton! While visiting, don't forget to stop at Waconah Falls, The Pines, and Holiday Brook Farm!

- "The property was very clean, easy to access and amazing with all the extras that most places don’t include. The water was really hot and it never ran out. The bed was out of this world comfortable. Property owner was very responsive and more than willing to help. Dogs welcome. I would definitely recommend this property. I hope to return sometime in the near future " - "This is an incredibly well renovated and extraordinarily comfortable house - one might never guess given the age of the property! It has been very tastefully decorated, and the thoughtfulness of the owner/operator is eminently evident. With the many (over 15) wonderful experiences I have had in recent year at VRBOs this one still stands out due to the extremely well stocked nature of the house in general, and the kitchen in particular! Additionally we were permitted to park a car in the abundantly large parking space outside of our reservation hours which made a HUGE difference in the convenience afforded to our point to point hiking the Appalachian Trail in the Cheshires. All of us who stayed would wholeheartedly recommend this as THE place to stay if hiking the Appalachian Trail in Massachusetts or theCheshires! "

Harbour House Inn B&B enjoys a location in Cheshire, 20 miles from Tanglewood and 25 miles from Norman Rockwell Museum. 19 miles from Cranwell Spa & Golf Club and 20 miles from Tanglewood Musical Center, the property offers ski storage space and a garden. The bed and breakfast provides rooms with air conditioning, free private parking, and free Wifi. At the bed and breakfast, all units have a wardrobe and a flat-screen TV. There's a private bathroom with bath in some units, along with bathrobes, a hair dryer, and free toiletries. At the bed and breakfast, every unit has bed linen and towels. Guests at the bed and breakfast will be able to enjoy activities in and around Cheshire, like fishing and hiking. Guests at Harbour House Inn B&B can enjoy skiing and cycling nearby, or make the most of the sun terrace. Bennington Battle Monument is 29 miles from the accommodation, while The Clark Art Institute is 15 miles away. Albany International Airport is 47 miles from the property.

- "This was the nicest inn we’ve ever stayed in; so charming and clean and the host was wonderful-we will definitely stay h" - "Great choice for “Inn to Inn” hiking on the AT." - "A perfect getaway. A lot to do in the Berkshires."

Bright and spacious, 25 ft ceiling, Post & Beam home on 25 private, hillside acres, nestled in the middle of the Berkshires, minutes from Lenox, Tanglewood, Williamstown, Pittsfield, Mount Greylock, Rail to Trails, Balance Rock State forest, the Appalachian Trail, skiing in Massachusetts (Jiminy Peak, Bosquet, Butternut) and Vermont (Bromley, Stratton), antiquing, orchards, and amazing BBQ at Biggin’s Diggins. 10 minutes to swimming and boating in Lake Pontoosuc, 8 minutes to skiing at Jiminy Peak and ropes adventures at Ramblewild. With 4 bedrooms (including a Bunk Room), the house can sleep 10 people in beds, and 12 including a pullout queen sofa bed.

Description:

As you drive up the long windy driveway of this private, secluded 25 acre property, you feel enveloped by the forest. When you near the top of the hill, the forest opens up to a contemporary mountain home. As you walk into the house thru the mud room, the Great Room opens before you with a soaring, 25ft ceiling, sunlight streaming in thru windows, skylights and sliders everywhere, and the rich smell of yellow pine. The entire house is walled with tongue-in-groove yellow pine, with giant wood beams that run the length of the house and equally large cross beams and exposed joists, making a lattice of wood from floor to ceiling. Comfortably furnished and well appointed with all the comforts of home, you have multiple ways and places to relax. You can flop down on the giant sectional and put your feet up, go upstairs to the balcony and stretch out with a book or a game, go down to the lower level lounge and watch a movie on the 65” Samsung TV, retreat to your bedroom and take a nap curled up with feather and down pillows, or sit on the deck and bird watch at one of the feeders.

Main Floor
The entire main floor is an open floor plan, with windows of all shapes and sizes, pine plank floors, and 4 sliders leading out to different parts of the huge deck. With the kitchen, living and dining areas open to each other, it lends perfectly to socializing and spending time with a group, whether you are on a multi-family holiday, a friends reunion or a single-family getaway. A fully appointed kitchen, with new high-end stainless steel appliances (GE Café 6-burner gas range/oven, Café Refrigerator, and a Bosch dishwasher), granite countertops, All Clad and Cuisinart cookware, Henkel cutlery, bakeware, serving platters, bowls and more, is ideal for making gourmet spreads to simple meals alike. People can eat at the large farm table (which can comfortably fit 10 or, with the extension, 12) in the dining area, on the screened in porch, or pull up a stool and sit at the eight foot island, perfect for socializing and helping with the meal prep. A big sectional faces a fully functional wood burning stove keeping you warm during those cold winter nights. And, for the more competitive types, there is a full-size foosball table with plenty of space around for spectators.

Second Floor
As you walk up the wide stairs, you pass by an enormous angular plate glass window giving you a view out front and (in Spring) the Robin’s nest with babies, that sit on the outside sill. At the top of the stairs is an upstairs loft area with a small sectional couch that turns into a queen size sofa bed. You can watch the large 65” Samsung TV or pick a book or puzzle to relax. Along the railing you get a full view of the main floor layout just before you enter the master/primary bedroom. As you walk in, you see the giant beams and a cathedral ceiling, a king size bed, a long bench under a wall of windows facing south west, and an en suite bathroom with a double sink vanity.

Lower level
As you walk downstairs from the main level, you move from soaring timbers to a cozy lounge. The lower level lounge has a large sectional that can seat 6 in front of the large screen tv, or play board games on the large coffee table. As you work your way back you find 2 queen bedrooms, one with a built-in bed, and the other an impressive sleigh bed. Walking down the short hall you pass the other full bath and head into the bunk room, with handmade, sturdy, built in bunk beds and plenty of drawers for clothing.

Amenities:
Every convenience of living at home is provided whether it is choosing from any variety of puzzles and boardgames, cotton sheets (flannel for winter!), new mattresses and feather pillows (hypo-allergenic too!), to Smart TV’s, high speed WiFi, Alexa for music, cable and streaming services (or use your own), soap/shampoo, hair dryers, iron/ironing board, towels, washer/dryer, dishwasher, Braun coffee brewer, Keurig coffee maker, toaster oven, food processor, pots, pans, blender, baking and serving dishes, knives and utensils. Basic spices and baking ingredients are available, as well as condiments (tho many prefer to buy their own). You need only bring or toiletries and any food!

Property
This striking contemporary house sits on 25 acres of very private woodland property, situated on the backside of Jiminy Peak, the largest ski mountain in Massachusetts. We abut 500 acres of private property and sit up the hill a couple hundred feet from the road, which makes it an exceptionally peaceful and quiet location. You are truly in nature. The sights and sounds of the forest are with you day and night, from the wind rustling the leaves and deer walking across the yard to the family of owls swooping from tree to tree and coyotes calling at night. We recently took down some trees to open up the space around the house, and create future space for more lawn and plantings, with the huge trees resting on the forest floor. The woods are lovely, looking densely packed from a distance but as you walk, you realize there is plenty of open space around you.

Location and Things to Do
Sadie’s Woods is the ideal location for the outdoor enthusiast, as well as those who enjoy cultural pursuits.
In winter: For skiing, we are less than 10 minutes from Jiminy Peak, and 45 mins or less to 4 other family ski mountains. For the more adventurous skiers, we are an ideal jumping off point for day trips to VT resorts Bromley and Mount Snow, a little more than an hour away.
In Spring, Summer and Fall: We are a 5 minute drive from Pittsfield state forest and Balance Rock State Park, and 15 mins to Appalachian Trail access, with lots of great hiking within minutes of the house. For bikers and walkers, it is only 6 minutes to the beginning of Ashuwillticook Rail Trail, one of the longest in MA. For fishing, water sports and swimming, Lake Pontoosuc is 10 mins away, and Cheshire reservoir is 15 mins. There are 3 golf courses within 10 miles.
The location is also perfect for those who want to enjoy culture and history from all parts of the Berkshires, from the Mass MoCA museum, Hancock Shaker Village and the Clark Art Institute, to music at Tanglewood or theater in Williamstown, being equidistant to both. On the way you go thru historic towns like Pittsfield, Lenox, and Adams (each with their own attractions). In each of these charming New England towns are fantastic food options for every meal.

- "We enjoyed this beautiful home for a break last week! From the minute we pulled off the main road we knew we were in for a special few days. The great room has large windows providing lots of sunlight and a panoramic view of the surrounding woods. The elevated deck was the perfect spot to enjoy my morning coffee and book-it was like being in a treehouse. The house is a quick drive to Tanglewood, the reason for our visit. The hosts, Kim and Chip have thought of everything: the house has tons of amenities, a full gourmet kitchen, huge sectional sofa and even a foosball table! It would be an ideal winter revisit for ski season (wood burning stove and that kitchen) or leaf peeping- with plenty of space to return with friends! "

Located in Adams, within 23 miles of Cranwell Spa & Golf Club and 23 miles of Tanglewood Musical Center, The Revival House provides accommodations with a shared lounge and free WiFi throughout the property as well as free private parking for guests who drive. The property is around 23 miles from Tanglewood, 25 miles from Bennington Battle Monument and 28 miles from Norman Rockwell Museum. The hotel features family rooms. The private bathroom is equipped with a shower, a hairdryer and slippers. Guest rooms at the hotel include air conditioning and a desk. You can play table tennis at The Revival House. The Clark Art Institute is 12 miles from the accommodation, while Southern Vermont College is 24 miles away. Albany International Airport is 48 miles from the property.

- "Interesting overnight stay in old home in the Berkshires" - "We enjoyed it and would like to go back again." - "We enjoyed our stay"

Private, unique getaway in the center of the Berkshires. We're a 3 minute walk to the Ashuwillticock rail trail. Situated on over 100 wooded acres with lots of walking trails, extraordinary trees, land forms and private seating areas and spaces to explore.

The cottage is a newly built. Super comfortable space above a stand alone 3 car garage. We have a private entry driveway and parking area exclusive to the cottage. Open floor plan with fun window seats, full kitchen and living room and full bath. It's a unique thoughtful design.

Radiant floor heat in the winter, central A.C. in the summer.

- "Great location, property and host. Very clean space. Lots to do around with great food options. Definitely coming back." - "From check-in to departure, this sweet, attractively appointed, large studio space, on beautiful grounds, in a great location was the perfect home base for an outstanding long weekend in the Berks. Would return in a heartbeat." - "We had a wonderful weekend at the Carriage House. The photos show the nice secluded location, but it is only a few turns from shopping centers, grocery stores, and downtown Pittsfield. The nearby rail trail is newly paved and a beautiful walk through the woods. The apartment has all necessities for a great getaway in the Berkshires!"

If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a guest house - since 1998.

PLEASE NOTE: It's an old building with an unusual layout, so please carefully read the description below.

Beautifully situated amidst horse farms on the scenic road to Mt Greylock. In the center of the Berkshires, 5 miles from Jiminy Peak ski area, 10 miles from South Williamstown, 15 miles from Tanglewood and Mass MoCA, and 20 miles from Jacob's Pillow. 5 miles to Pittsfield and the Berkshire Mall. Private garden. 5 acres of property in the back where horses graze, and alpacas, donkeys and other friendly animals next door.

Everything is provided: fully-furnished mostly with antiques. Bedspreads, linens, blankets, pillows, towels, iron and ironing board. SMALL KITCHEN with mini stove/oven, refrigerator, microwave, Keurig coffeemaker with assortment of coffee, tea and hot chocolate, pots and pans, dishes, cutlery, etc. Broadband internet and TV with Netflix, Hulu and other streaming options included.

There are 2 floors. The first floor is the old classroom with old desks. There is also a trundle bed which can be used as 2 twins. The bathroom is on the first floor. The 2nd floor is like a studio apartment - with a queen bed and a twin bed and the small kitchen. PLEASE NOTE: There is one bathroom, on first floor.

Ideal for a romantic getaway or for a family of 4-5. A fee of $25/night applies for additional adults after the first two (limit of 4 adults total). No extra charge for children. Please indicate the number of children in your message to us, but select 0 children in the pull-down menu so that you are not charged.

The Old Stone School is available to rent 12 months a year. Each season has it's benefits:

SPRING - Trees arise from winter sporing their fleeting Spring green color, daffodils, tulips, hiking trails are open, enjoy the warm weather after a long winter! Calves appear on the hill behind the schoolhouse.

SUMMER - Flowers blooming, berries to pick, outdoor activities nearby, culture everywhere - Tanglewood, Jacob's Pillow, Barrington Stage, Clark Art Museum, MassMoCA, Williams College Museum of Art, etc.

FALL - Enjoy the kaleidoscope of Fall colors covering the hills behind the schoolhouse. Hike Mt. Greylock - short and long hikes. Go the top and check out Bascom Lodge - a stop on the Appalachian Trail.

WINTER - Jiminy Peak is less than 10 mins. away.Ski or snow tube at Bousquet is 20 mins. away. Cross country Ski in the fields out back or go to Hilltop Orchards in Richmond or Notchview in Windsor.

- "Our stay at this historic schoolhouse was terrific. The owner was very welcoming and helpful. We slept well there - as the two available large rooms up and down afforded flexible sleep areas. Beds comfy. The kitchen was well equipped and the amenities such as foil, plastic wrap, tea, a Keurig machine, extra paper plates etc made our stay very convenient. The history of the place is fascinating. Many thanks!" - "This charming converted schoolhouse is well-supplied for the present day while reminding you of a bygone age. It's set among beautiful rural woods and pastures, private, but with ideal access to local attractions south, like Stockbridge and Lenox or north, like Williamstown and North Adams. The owners are extremely helpful and friendly, and they also simply allow you to enjoy your stay. A great place!"

Come and enjoy the many adventures and activities that The Berkshires in Massachusetts has to offer. This cute 2 bedroom ranch is located in the quaint town of Adams at the base of Mt. Greylock. You can enjoy the many outdoor activities year round right out the back door. Play a round of gold at a nearby golf course, Hiking trails only steps away, MTB trails and the Ashuwillticook Rail Trail all within a mile, as well as many back roads to explore on your road bike. Snowshoe or ski Mt. Greylock in the winter months and leaf peep and hike during the Fall. Visit a museum or see a dance troupe or play at one of the many Theaters in the area. Enjoy local musicians in one of the many local parks that host Music in the Park or catch a concert at Tanglewood or MassMoca or the Newly opened Adams Theater. There are many museums in the area for young and old along with summer fun in town and in the surrounding towns. Bring the little ones and enjoy a picnic on top of Mt. Greylock, a swim at Windsor Lake or a little splash time at the free splash pad just 5 minutes away.

PET FEE: Please indicate if you are traveling with your pet(s). There is an additional set rate pet fee charge of $100.00 to cover the the additional cleaning costs.

Please indicate the number and type/size of pets upon booking, maximum pets allowed is 2, additional fee for more upon approval.

Let’s keep the Greylock Getaway pet friendly. I know I loved being able to travel with my pet, and I appreciate people who allowed me to bring him along and I understand the extra costs that come along with it, but he was worth it. I’m sure yours are too. Neighborhood and trails at the Greylock Glen are very pet friendly.

10 min drive to Windsor Lake in North Adams to enjoy fishing, swimming and Kayaking and 10 minutes South to Cheshire lake for kayaking and fishing. Enjoy Tanglewood, MassMoca, Clark Art, or one of the many other museums or theaters in the area as well. You will never be short on things to do in the Berkshires.

A 5 min drive to North Adams, 10 min to Cheshire, 15 to Williamstown, 20 min to Pittsfield, 40 min to Tanglewood, 35 min to Jiminey Peak Ski Area.

Check us out on Facebook TheGreylockGetaway to see what is happening in town and around the area.

*Please be aware this home has stairs, the front deck has 4 steps, back deck has 3 steps, same level access from lower level driveway or one full flight of stairs to main level living space from lower level family room (futon sleeping area), second bathroom/laundry room and extra bonus room on lower level.

* During the summer months, lawn care is done weekly. If you are staying for a full week this may fall on one of the days you will be there. You will get notice of that day. Snow removal is done as needed. Extra shovels and salt are provided for your use.

*Trash removal is done on Wednesday, Thursday or Saturday as needed. If it falls on a day you are occupying the home you will be notified ahead of time that I will be stopping by for a trash pickup.

** I No longer accept monthly long term rentals, maximum stay 2 -3 weeks unless approved for a longer stay.

***This home is protected by a WYZE security camera outside the home in driveways only.

- "Julie was very attentive in communicating with us and providing details of the home and surrounding area. Close to Mass MOCA and Clark Art Institute (short drive), sweet clean home. I came with a friend but had a nice selection of toys/games for young kids and a fenced in yard with a play area/jungle gym." - "We had a fantastic stay in Adams for a family reunion. This house was perfectly located right by Mount Greylock trailheads and Pecks Falls. Our Great Grandmother used to live in a house down the street so this was a wonderful trip down memory lane for us! Julie was so helpful and kindly left extra dog towels and bowls out! The fenced in backyard was super convenient and we loved all of the patio furniture!"

Newly renovated, one level house with 2 rooms with king sized beds, 1 queen size sleeper sofa. Fully furnished kitchen, new bathroom with tub/shower. Washer, dryer, electric fireplace, deck, and hot tub. Fire pit, horseshoes, walking trails, use of field, and access to adjacent garden center full of colorful shrubs and perennials.

- "It was nice even in the rain." - "The listing doesn't do justice to this place. The house is cozy, well maintained and clean, everything works. The location is great and there is a huge backyard to explore. Communication with Susan was great and she was very responsive and nice, like a true friend. We assisted to a wedding nearby and we took advantage to stay a few more days and having a great time. A beautiful place and a great house to come back...Truly recommended."

2 MIN TO JIMINY PEAK - right down the road and next door to RAMBLEWILD-
#1 AERIAL ADVENTURE PARK IN THE BERKSHIRES! Close to Lenox and Williamstown! Reduced rates. Great for 2 families (max 8 persons!) Come and enjoy our beautiful mountain retreat - A home for every season. This charming and secluded home away from home is a wonderful place for family, friends and romance. Only 2 minutes from Jiminy Peak, 15 min to Williamstown and 25 minutes to Lenox!! Book now!!! House comfortably fits 2 families with small children- see reviews

With over 2200 square feet, this beautiful secluded house with beautiful mountain views has plenty of space for everyone yet a very cozy feel. Each one of the 3 large bedrooms has walk-in closets and beautiful wood furnishings. The master suite has a king size bed and matching furniture with a 50” Samsung LCD HDTV. The attached master bathroom has a huge Jacuzzi tub for two. Step out onto the balcony from the living room for a magnificent open view of the mountains. Enjoy a movie on your 65” Samsung smart HDTV while enjoying the heat from the wood-burning stove. The enclosed basement can be used as a playroom or den with a bar and bar stools, an office with a desk and new HP printer, or as a closed-off 4th bedroom with a couch that opens up into a queen sized bed. Another Samsung 50” Smart TV is there. Explore the 16 acres of trails on the property and hike your way to the golf course in the back. If you have kids, there are swings and slides on the property for their enjoyment. There's also an attached 2 car garage so that you can come directly into the warm house after a long day of skiing.

There is also a fully stocked kitchen with all new appliances (bought in 2024) and a dining room which seats 8 persons. The laundry room also has a new washer and dryer.

And don't forget that just 2 miles down the road is Jiminy Peak - offering skiing and snowboarding day and night in the winter and mountain coaster and rides in summer. We are located about 25 minutes from Tanglewood. Or drive ten minutes down the road to the Clark Museum in Williamstown and enjoy some Monet and Renoir. Or fifteen minutes down the other direction to the city of Pittsfield for some wonderful restaurants and shops- as well as a beautiful lake for boating and swimming. And don't forget that we are only 2.5 hrs from NYC.

House is disinfected and sanitized after every guest by housekeeper who wears mask and gloves. No Contact check-in and check-out.

Keywords: House, Jiminy Peak, Berkshires, ski, hike, Lenox, Williamstown, Pittsfield, Hancock, Mountain, secluded, Lanesboro

- "Great experience. Deborah was great to deal with. The house was everything it was described? Definitely go back again!" - "We highly recommend this house. The accommodations and the many amenities helped make our family’s stay comfortable and enjoyable. The house is centrally located between Pittsfield, MA and Williamstown, MA. This made it convenient for our family to attend our daughter’s commencement activities at Williams College, plus expanded our choices in shopping & restaurants. Also, the host was very responsive to our questions prior to our arrival. Thanks for your hospitality Debbie :-) The ONLY recommendation for improvement would be to better post the address sign on the driveway’s entrance to the property. The sign was propped up on the ground which makes it difficult to see, especially at night."

This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four separate cute suites. Newly updated kitchen, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife.

Follow us on IG @SecondDropFarm

Both myself and Samantha are always available to answer any questions about the unit, property or surrounding area.

Mount Greylock State Reservation: 1.4 miles
Jiminy Peak Resort: 5.2 miles
Pontoosucc Lake: 3.4 miles
Mass MOCA: 17 miles
Wachonah Falls State Park: 11 miles
The Clarke: 14 miles
Naumkeag House and Gardens: 20 miles
Tanglewood: 15 miles
Bash Bish Falls: 43 miles

Target: 4.7 miles
Starbucks: 4.7 miles
Dunkin donuts: 3.2 miles
Market 32 Grocery: 5.9 miles
Stop and Shop Grocery: 5.5 miles
Guidos Fresh Marketplace: 9.4 miles

- "Location was perfect for the occasion we were attending. Property just as advertised. Owner very accessible and friendly." - "Great place , comfortable and spacious" - "Very clean Unique step back in time with the the hand shrewd beams" - "We wanted a couple night getaway for our anniversary. This apartment was very clean, rustic, quaint and romantic. It was perfect. The bed was comfortable. Communication was great. We enjoyed the walk around the farm."

This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four separate cute suites. Newly updated kitchen, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife.

Follow us on IG @SecondDropFarm

Both myself and Samantha are always available to answer any questions about the unit, property or surrounding area.

Mount Greylock State Reservation: 1.4 miles
Jiminy Peak Resort: 5.2 miles
Pontoosucc Lake: 3.4 miles
Mass MOCA: 17 miles
Wachonah Falls State Park: 11 miles
The Clarke: 14 miles
Naumkeag House and Gardens: 20 miles
Tanglewood: 15 miles
Bash Bish Falls: 43 miles

Target: 4.7 miles
Starbucks: 4.7 miles
Dunkin donuts: 3.2 miles
Market 32 Grocery: 5.9 miles
Stop and Shop Grocery: 5.5 miles
Guidos Fresh Marketplace: 9.4 miles

Air Conditioner • Child Friendly • Other • Fireplace/Heating • Internet • Security/Safety • Wellness Facilities • Parking • Tv • Balcony/Terrace • Kitchen

Your Cozy Berkshires Getaway Awaits!

Escape to the serene beauty of the Berkshires! Nestled in a peaceful, family-friendly neighborhood with breathtaking countryside and mountain views, our home is perfect for families, couples, or friend groups seeking relaxation or adventure.

Cozy spaces for every season: Warm up by the indoor fireplace or gather in Adirondack chairs around the outdoor fire pit (seasonal).
Winter fun: Explore nearby trails for hiking, snowshoeing, or relax with board games and hot cocoa after a day at local ski slopes.
Stay connected: High-speed Wi-Fi and smart TVs for streaming your favorites.
Family-friendly touches: Bunk beds, toys, books, children's tableware, and play areas.
Modern conveniences: Fully-stocked updated kitchen and laundry appliances.

Comfortable living spaces
→ Our home is designed for relaxing and creating memories.
→ The living room features a fireplace, Roku Smart TV, books, games, dedicated workspace, and even a digital piano.
→ The dining room, with its large windows facing the garden and mountains, is perfect for families. It includes a smaller children’s dining table and a play kitchen for creative fun
→ Whether you’re enjoying a quiet evening or a lively game night, these spaces invite you to make them your own.

Fully equipped kitchen
Cook up a storm or whip up a quick meal in our modern chef’s kitchen:
→ Sleek, modern appliances including range/oven, fridge, dishwasher, toaster oven with air fryer, and Keurig coffee maker
→ Essentials like cooking oil and spices included
→ Plenty of cookware and dishes for your culinary adventures
→ Cozy breakfast bar with garden views

Restful bedrooms and clean bathrooms:
→ Master Bedroom: King bed, dedicated workspace, and smart TV.
→ Queen Bedroom: Stunning mountain views and cozy sitting area.
→ Full Bedroom: Full bed and dedicated workspace
→ Children’s Room: Twin bunk beds, toys, and books.
→ Upstairs bathroom has a full tub, downstairs bathroom has a shower stall

All beds feature memory foam mattresses for a great night’s sleep. Bedrooms have closets with hangers and drawers for your personal items.

Bathrooms are stocked with towels, soap/shampoo, and even children’s bath toys for added convenience.

Outdoor winter wonderland
→ In summer, explore our landscaped, edible garden, where you can pick fresh chives, blueberries, gooseberries, black raspberries, apples, and peaches (seasonal)
→ While our garden sleeps for the winter, the outdoor space transforms into a haven for snowy fun!
→ Enjoy morning coffee on the patio or sip wine surrounded by mountain views at sunset - in any season.
→ On clear nights, enjoy stargazing and even the occasional aurora borealis sighting!

- "Lovely home and convenient location. Host very helpful." - "We had a great stay! We all needed a spacious and comfy home with a fireplace- and that is what we got. it had everything we needed and Amar is so responsive. I offered some unsolicited suggestions to make even better? He was appreciative. there was a hiccup with an appliance and he was on it asap! almost do not want to review it - so that we can hide this jewel!" - "We were two families of four, both with kids aged 4 and 6 and we loved this home! The place is cozy and has all of the touches that make it feel like home. Little things like hooks for towels and phone chargers make a big difference! Extra bonus for all of the kids’ toys! The house is very clean and well-appointed. My husband wants me to mention that the fire building gear was excellent. The owner is very helpful and communicative. Checking in and out is easy. We enjoyed exploring Mass MOCA, skiing at Jiminy Peak and a visit to Susan B Anthony’s house. We also enjoyed local restaurants!! Great house and great experience!"

*All bookings are subject to COVID-19 regulations by the state of Massachusetts.

*Until regulations change, all guests coming from out-of-state are asked to observe a 14-day self-quarantine while at Brooksong. Please contact for more information.

*Cleaning staff is working double to sanitize as thoroughly as possible. I also try to block off at least 2 days between each booking for safety reasons.

Located in the lovely Berkshire mountains, part of this bright, sprawling property was built in 1866 as a schoolhouse. It has since retained its historic charm while including all the updated comforts of home. Play pool, sip cocktails at the antique 1920s bar, sing songs around the outdoor fire pit, cook dinner in the huge kitchen or enjoy grilling on the porch in the sun. Skiers and hikers will love the area, and with over five acres of wooded land to explore, the property is perfect for a vacation with friends or family reunion.

Brooksong is an incredibly unique space, full of historical flourishes and quirks, and the house has been entirely renovated with comfort in mind. Lovingly maintained, Brooksong has the ideal combination of classic and modern decor. The house comfortably sleeps ten so you can enjoy a great weekend in the Berkshire countryside with the people you care about.

In addition to Brooksong's five acres of land, the Berkshires have many other beautiful woods and meadows to hike in. Wahconah Falls State Park is just up the road, and the dramatic waterfall is definitely worth checking out. Skiers should note that there are several places nearby to hit the slopes; the closest, Jiminy Peak, is about 25 minutes away. For some culture, the Massachusetts Museum of Contemporary Art is a half hour's drive from the house. The town of Dalton has some quaint restaurants and shops, and the Berkshires are renowned for their array of adorable villages and hamlets to browse. The town of Pittsfield is about 10 minutes away, and has all the strip mall options you could ask for: Stop & Shop, Home Depot, Target, etc. In other words, you'll be secluded but not cut off from civilization! Holiday Farms is a great organic farm just up the road and there are many similar establishments nearby, so I highly recommend trying some local meat, dairy and produce.

*The following would not usually be included here, but we live in strange times. Brooksong has few neighbors and they are separated from the property by farmland and woods. Our water comes from a well. Self-sustaining farms are within walking distance. The nearest hospital is BMC, about 12 minutes away by car, and there are many places nearby still open to get supplies, as well as grocery delivery in the area. The WiFi is excellent and all the infrastructure necessities of the house, like propane, are constantly maintained. My house manager is on call 24/7 for any problems. Honestly, there are few better places to get away from crowded areas and ride out the current situation than Brooksong. We will do our best to make sure you feel safe and comfortable during this stressful time.

- "Super clean and beautifully laid out and decorated " - "Had fun here for a guys weekend trip. Good location and fun comfortable house." - "This house was just excellent, from check-in to check-out. Communication with Sulmone was great. The property is private with farms surrounding the property, a great all-around place for a large family or families to stay. The drawers and cabinets were well stocked with all the utensils, pots, and pans you will need for cooking and eating in. The beds and linens were very comfortable and made sleeping easy. We stay at many VRBOs and I have to say this one was one of the top places yet. The radiant floor heating warmed the house up to take the chill out, unlike forced hot air to dry the air out. The yard has a nice fire pit with no worries. Bottom line you need to make an effort to stay at this house to really enjoy it and experience a great relaxing property. Stores are close enough if you forget something or need to pick up groceries. 5 Stars out of 5 for sure!"

This lovely studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four cute apartments. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife.
*Check out our other rentals on our profile!*

Follow us on IG @SecondDropFarm

- "We really enjoyed our overnight stay while visiting Williams College with our son. Very comfy beds, easy to use tv, nice kitchen. Would definitely stay again." - "Gem of a property- great location & clean." - "Love the location, super convenient to Greylock. Being a studio with the kitchen open to the bedroom make sure everybody you're with is on the same schedule. It was clean, had most of what I needed there and plenty of space. Will definitely return to this or one of their other units in the future."

This lovely studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four cute apartments. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife.
*Check out our other rentals on our profile!*

Follow us on IG @SecondDropFarm

Kitchen • Fireplace/Heating • Security/Safety • Other • Child Friendly • Balcony/Terrace • Tv • Air Conditioner • Internet • Wellness Facilities • Laundry • Parking

Our 6BR home is super comfortable, designed for multiple families to share (max 14 guests), up to date, and just minutes from the greatest sites in the Berkshires. Jiminy Peak Mountain is 7 minutes from the house, Tanglewood is 15 minutes away.

The house is big, and there are plenty of separate areas for people to hang out, so even with large groups you will not feel on top of each other.

We have a hiking trail, 4 fireplaces, an outdoor firepit, a stream on the property, and all the nature you can handle. Free firewood is included in your stay.

Additional features: Sauna, Jacuzzi, Ping Pong, kids games, Giant Jenga, multiple hangout rooms, high speed internet, wifi, and tremendous privacy. Our family uses it all the time, so its kept up very nicely.

Our great caretaker lives just down the block, and will welcome you when you arrive to hand you the keys and give you a tour of the house.

- "We were provided an organized list of instructions for checking in/out as well as things to do in the area for different groups/situations before our stay. Jim the caretaker was great in providing instructions when checking-in, and both Jim and Jon were great when it came to answering any questions in a timely manner and also making sure we were taken care of. The property itself is very warm and inviting, the amount of windows/sunlight and areas to lounge as a group is awesome! We especially thought the kitchen was stocked well with everything you would need to cook meals for large groups and was fun to use. The area around the property is very picturesque and peaceful, but also feels like you can hang with your friends and make some noise (not too much) without disturbing the neighbors, which, we are a loud (in speaking volume) group, so that was definitely great to not have to worry about disturbing anyone. We really loved our stay and would definitely look to come back to the property if we find ourselves in the Berkshires again."

Bright and clean apartment on flower farm in the mountains

This bright 1BR/1BA is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four cute apartments. Newly updated kitchen, floors, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife.

Follow us on IG @SecondDropFarm

Both myself and Samantha are always available to answer any questions about the unit, property or surrounding area.

Mount Greylock State Reservation: 1.4 miles
Jiminy Peak Resort: 5.2 miles
Pontoosucc Lake: 3.4 miles
Mass MOCA: 17 miles
Wachonah Falls State Park: 11 miles
The Clarke: 14 miles
Naumkeag House and Gardens: 20 miles
Tanglewood: 15 miles
Bash Bish Falls: 43 miles

Target: 4.7 miles
Starbucks: 4.7 miles
Dunkin donuts: 3.2 miles
Market 32 Grocery: 5.9 miles
Stop and Shop Grocery: 5.5 miles
Guidos Fresh Marketplace: 9.4 miles

Parking right outside rental

- "Property is in a converted farmhouse. Rooms were spacious and clean with simple decor. We were in town for a wedding so needed a simple base to work from, but the size and location would lend itself well for exploring the area in an extended stay. Patrick the host was amazing, and very responsive to our questions. Would certainly stay there again." - "Very nice. Attending a wedding in the area and really needed a place to get dressed and return to sleep. This fit the bill perfectly. Clean and comfortable we enjoyed our visit. Need to come back and visit the many sites in the area."

12 MINUTES TO JIMINY PEAK
Feel like you have entered your own oasis in this charming retreat. A hidden gem set far back from the road, tucked away on almost 3 acres of privacy with lush nature This 3 BR, 1.5 bath home seamlessly blends modern updates with mid-century decor, and features a brand new spacious deck to relax and take in the unobstructed mountain views. Centrally located; 6 minutes to Mt Greylock, 4 minutes to Cheshire Lake and the Ashuwillticock Rail Trail.

If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.

This quiet rural community is a beautiful peaceful place in the heart of The Berkshires.

Guests have full use of the property excluding a couple locked closets for owners storage

The interior of the home has been updated in a stylish, sleek mid century modern decor and vibe with all modern comforts and conveniences.

This bright and airy home features a spacious living room with a large comfy sectional, electric fireplace, and a magnificent picture window for an up close and personal view of the changing seasons in the Berkshires.

Our well equipped kitchen boasts plenty of space for preparing meals at home and a dining table for 6. A gas grill is also provided, so guests may barbecue then dine under the stars on the beautiful new deck!

The primary bedroom with a queen bed, work-from-home private office, and full bathroom with combo tub/shower are located on the main floor of this home. The additional two bedrooms, both with queen beds, and half bath are located on the second floor. A futon style sofa is also located in one of the bedrooms to accommodate guests.

The garage is available to store ski equipment at the end of a day on the slopes or kayaks after paddling at nearby Cheshire Lake.

Central heating, a back up generator, and an electric fireplace make for a warm, cozy stay in the fall and winter months- while multiple window unit air conditioners help cool things off in the heat of the summer.

The yard is beautiful and spacious with plenty of room for lawn games. If that's not your thing, you can swing in the shade on the tree swing and watch the bunnies play in the grass or catch some rays on the lounge chairs provided on the deck.
Gather around the new outdoor fire pit and toast marshmallows while sharing ghost stories under the stars.

Located in the small town of Lanesboro minutes from Cheshire Lake, Pontoosac Lake, Mt Greylock and Lakeview Apple Orchard. A short drive north takes you to beautiful Williamstown and Mass MoCA in North Adams. Venture south to visit the quaint towns of Lenox and Stockbridge.

Skiers!! 12 minutes to Jiminy Peak, 45 minutes to Berkshire East, 20 minutes to Bousquet, 45 minutes to Butternut Ski Area.

Having a car will greatly enhance your ability to explore the Berkshires effectively.

NOTE TO GUESTS: This property is loved and used by the homeowner. It is shared with guests who will love and care for the property with the understanding that it is someone's home.

LOCATION: This quiet rural community is a beautiful peaceful place in the heart of The Berkshires. A 10 minute drive from Pittsfield, a major cultural and shopping destination and now home to the newly launched Berkshire Flyer Amtrak train - ideal for Manhattanites from Penn Station.
PETS: A dog may be allowed with owner approval. Reach out with info about your pet prior to booking including size, age, breed and overall temperament. A $100 pet fee will be inccured upon pet approval and booking. No multiples.
PARKING: Free parking on premises. Please no more than 3 cars during snow season. This allows for adequate snow removal if there is a storm during your stay.
*The house has high speed internet/wifi and 2 smart TV’s that will have basic cable and streaming service apps already installed on them. (You’ll log into your own Hulu, Netflix, Prime, YouTube, etc accounts.)

**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

- "We had a wonderful time here! The property was well cared for and the hosts were very responsive. It’s in a great location with easy access to many attractions. We would definitely stay here again in the future." - "My husband and I attended my niece’s wedding, the house had everything we needed to make our stay enjoyable. We were able to bring our little Scotty did Gracie who loved it too" - "warm n comfy home away from home. close enough to town for convenience , yet secluded. clean. just one full bath….downstairs. first time in a vrbo. it’s a great option for spending time in a more centralized area."

Stay in one of the best preserved historical home that's now a private art galley in downtown Adams. Walk to Adams Theater, Firehouse Cafe, AJ's Trail Pub after a day of hiking or visit to MASS MoCA or the Clark Art. Marvel at the detail woodwork or the antique opium day day and actually sleep in it as an overflow twin bed. Private bedroom has a queen bed and a half bath Modern day comfort, art, architecture in a downtown location in the Berkshires! Situated between North and South Berkshires and within an easy drive to Stockbridge, Great Barrington in southern Berkshires and still within 15 minutes to MASS MoCA and Clark Art. This is a large apartment however it's not intended to accommodate more than three people (a queen and a twin bed total).

- "We stayed in this beautiful penthouse for an overnight get away- we both walked in and were just in love. The high ceilings and tons of windows made it so open feeling. Stunning place!" - "We had a lovely time and Lea was a great and hospitable host. Awesome spot!!" - "Adams is a beautiful town and looks and feels like the appalachian trail! " - "We had a wonderful relaxing stay in this gorgeous place. The listing is just as described, natural light filled, high ceilings, on the top floor, comfortable bedding, and a thoughtful host. Lea left the A/C on, a bottle of water in the fridge, lots of good coffee, and even some hot cocoa packets for our son. The boba shop right downstairs was awesome and had fun gift items. There is a diner next door and some fantastic restaurants 15-20 minutes away. Very convenient to Mass MOCA and Williamstown. The rail trail and visitor center is just outside the back door. This is a very safe quiet neighborhood, there's not a lot going on in Adams but it's a great spot to explore the northern Berkshires area."

15 MINUTES TO JIMINY PEAK
Welcome to your serene retreat nestled on 4 private acres. This newly renovated 4BR/2.5BA home offers breathtaking views of both the tranquil lake and majestic mountains. Step inside and discover a chef's dream kitchen, fully equipped with top-of-the-line appliances and ample space for culinary creativity. After a day of adventure, unwind in the luxurious soaking tub, or relax next to the fire.

If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.

This beautiful lake front property in Cheshire provides breathtaking views year round. The large property provides plenty of privacy for a relaxing stay.

Guests have access to the entire home. A golf cart is also available for an easy ride down to the lakefront.

For chefs enjoying the bounty of the Berkshires & the Hudson Valley, the main floor of this home features a fully stocked chef’s kitchen with quartz countertops, professional cooktop, and wall oven. There is even a sous vide immersion circulator for your use! A Nespresso coffee/cappuccino machine is provided to make your favorite coffee shop beverage at home!

A dining area in the kitchen provides counter seating for four guests while the main dining room seats an additional six people. Cozy up in the living room with a gas fireplace and a 65” smart TV with surround sound. The first floor also contains a half bath.

The primary suite features a balcony overlooking the property and huge windows offering views of the lake and mountains beyond. Sleep soundly on a King memory foam mattresses and crisp white sheets. Enjoy the soaking tub in the primary bath with views of the lake.

The three additional bedrooms offer plenty of room for guests: 1 Queen bed, 1 bunk bed with Full size bottom bunk and twin on top, as well as an office with a pull out Queen bed. A full guest bath with a tub/shower combo is on the second floor.

In the basement, you’ll find ping pong and air hockey tables, plus a washer/dryer.

2 direct routes from the property to the lake allow for easy access for guests. Enjoy outdoor games on the large, flat lawn and take one of the two kayaks for a ride around the lake. Dine outside with the large outdoor dining set that seats a total of 8 guests.

Cheshire is a quiet, rural community. We like to visit four nearby farms: Lakeview Orchard offers seasonal pick your own fruit and amazing cider donuts. Mountain View Farm has pick your own berries. You can buy fresh pastured eggs at Square Roots Farm, and Whitney's Farm Market has a small grocery with local produce - most notably their own tomatoes and corn.

The Ashuwillticook Rail Trail, winding 13 miles along Cheshire Lake between Pittsfield and Adams, is just down the road. For the more adventurous, an Appalachian Trail trailhead is 5 minutes away in the town of Cheshire. Winter sports are close by with Jiminy Peak a 15 minute drive away. We are also close to southern Vermont resorts, with Mt. Snow and Stratton about an hour’s drive. Or, walk right outside and sled down the hill in our backyard.

The home is close to major cultural institutions, such as the Berkshire Museum (15 minutes), Mass MoCA (20 minutes), the Clark Art Institute (30 minutes), and Tanglewood (30 minutes).

This home truly has everything you need!

Having a car will greatly enhance your ability to explore the Berkshires effectively.

LOCATION: This beautiful lake front property in Cheshire provides breathtaking views year round. The large property provides plenty of privacy for a relaxing stay.

PETS: Dog allowed with owner approval, no dogs under 2 years old. Please reach out for owner approval on the dog prior to booking. No multiples. $100 fee will be applied if approved.

PARKING: The house features a 2-car garage for your use. Electric cars are welcome, a 40-amp level 2 charger is provided for guest use.

LAKE INFO: Stretching across nearly 418 acres, Cheshire Reservoir (also known as Hoosac Lake) is one of the largest bodies of water in the Berkshires, offering wide-open space for boating, fishing, kayaking, and lakeside lounging. With a maximum depth of around 26 feet, the reservoir is a favorite for anglers targeting bass, pickerel, and perch. Divided into three basins, it offers a mix of recreational and quieter zones, making it ideal for everything from water sports to peaceful paddles.
*All guests who wish to use the golf cart and kayaks will need to sign a waiver in advance of their stay. Management will reach out for signatures prior to arrival for a seamless experience.

*There is a steep hill from the home, down to the lake. Lake is swimmable in season, there are weeds in the lake. Owners have cleared weeds around the dock area for swimming.

*Enjoy fast cable Internet and excellent cell service with AT&T, Verizon, and T-Mobile.

**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

- "The house was beautiful, clean, and so well stocked with everything we needed. Our kids loved the bunk beds and kayaking around the lake. The view and property was amazing and so peaceful! Communication with the property manager with super quick and easy. The bike path is really close and nice! Quick ride to Mass Moca and other things to do. Overall wonderful trip!" - "We rented for a family birthday celebration. This home had everything to make our stay comfortable for all ages. Highly recommend!"

Expansive Berkshire family home situated on four pastoral acres. The home features post-and-beam primary with 4-BRs, lofted living room with desk and daybed, basement TV Room, spacious kitchen. In-law suite features 2-BRs, second full kitchen, living room, dining area, offering ample space for extended families. Amenities include a pool (seasonal), a hot tub & fire pit. Nearby attractions include Jiminy Peak, Mt. Greylock, Tanglewood, Ramblewild, Ashuwillticook Rail Trail and MASS MoCA.

Outdoor activities are very plentiful here in the Berkshires of Massachusetts! Several lakes nearby provide many opportunities for swimming, fishing, kayaking, canoeing, and jet & water skiing, and more! Better yet, you can rent a Pontoon Boat and party away the day on Pontoosuc Lake, only 5 miles from this AMAZING property! Other top reasons to visit our beloved Berkshires: Scenic beauty, charming small towns, and cultural enrichment.

Guests have access to the entire house and all four acres. A private 15 x 30-foot outdoor pool (4 feet deep) and a hot tub are also available.

The Dining Room features a large wood-burning fireplace, there's a wood-burning stove in the living room, and there is also an outdoor fire pit. A few pieces of firewood are provided to get you started!

Additional sleeping space: There's a Twin Day Bed + a Twin Trundle Bed underneath in the Loft area above the main living-room.

Coffee maker: There's 2 drip pot coffee makers at the house.

Outdoor/Indoor Games: The house is chock full of popular outdoor games and equipment, including Volleyball, Badminton, Pickleball, Basketball, and Croquet. The indoor Game Room is equipped with a Ping-Pong Table, Shuffleboard, and Foosball.

About the pool: The pool typically opens around Memorial Day and is closed around the beginning of October, weather depending.

Local Discounts for our Guests: We have secured 10%-Discounts for our guests at Berkshire U-Drive Boat Rentals, Berkshire Bike & Board, and the Lanesborough Local General Store, and the "Elle Day Spa" has put together special packages for our guests during their visit. All of these are located within 3.5 to 5 miles of the property. Discount access codes provided upon booking so guests can pre-book their rentals or spa packages =)

Wildlife: This is a home in a rural part of the country. You may see deer, coyotes, foxes, and bears. Please be mindful of your surroundings, and avoid leaving out food and trash. There are a couple of super cute Highland cows next door that you may see come to the property line fence. Please do not touch or feed them.

Weather: In the winter, there will be snow, ice, and occasional snowstorms. Even though our home is easily accessible, it is always helpful to have 4WD to drive in the area in the winter.

Air conditioning: Please mind that AC is seasonal and available during the summer months only.

Power and Internet: It is not uncommon to lose power or internet during inclement weather. We do not issue refunds for the loss of power or internet out of our control.

Pet Friendly: We can host up to 2 dogs. The pet fee is $100 for one dog and $150 for two dogs. We ask that dogs are kept on a leash while outside the property and about the neighborhood, for everyone's comfort. Please remember to clean up after your pets and mind that additional fees for pup-related damages may apply! Dogs are not allowed in the pool. Finally, unfortunately we cannot host cats or other furry animals due to potential allergy issues.

Strict no smoking, no parties, no fireworks. Please mind that the noise ordinance is 10 PM. Other house rules will be on arrival guide.

Please mind that you must be 25 years old to book, and at least one person 25 years old must remain during the stay.

Cancellation Policy: We cannot make any exceptions to our cancellation policy. Please consider traveler's insurance.

- "I cannot say enough about our family vacation to this location. Huge home with so much space for everyone! We had 9 family members stay this past week and we had the best time enjoying the fire pit, the hot tub, family game room, and the expansive yard for playing out door games. The kitchen (and second kitchen) were amazing, had everything we needed and then some plus there was a large grill available for our seafood dinner night! Badminton, croquet, ping pong, foosball, shuffleboard, basketball, pool, volleyball. I could go on, however, the best part of this entire trip was the property manager, Stacey. She went out of her way to accommodate our every request, providing us with special local opportunities and being readily available at any time. The house was extremely clean, beds so very comfortable, and we loved the audio system that went throughout the house and outside! Do not miss an opportunity to stay here!"

9 MINUTES TO JIMINY PEAK SKI RESORT
This centrally located property at the base of Mount Greylock offers luxury and tranquility on 60 private acres with sweeping mountain views. Nestled amidst a botanical garden setting, this 3-bed, 3.5-bath haven boasts amenities including a heated pool, hot tub, central AC, covered walk-around deck and full gym. Enjoy 40 wooded acres, a pond, meadow, hiking trails, and year-round stream. It's your retreat in nature's embrace.

If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.

Lanesborough is a quiet, rural community. There are horses next door, visible from the home.

Guests have private access to the entire home, gardens, and property.

The home is a contemporary construction, completed in 2019. The open-plan living space features a cozy living room adorned with a gas fireplace, perfect for guests to unwind and relax. The kitchen is a chef's dream, outfitted with a Nespresso machine, fondue pot, Dutch oven, cocktail bar cart, outdoor grill, and outdoor pizza oven.

A dedicated full laundry room on the main floor awaits, complete with a washer and dryer available for guest convenience.

The first-floor primary bedroom boasts a luxurious King bed, an en-suite bathroom adorned with a soaking tub, double vanities, and a separate walk-in shower. Double doors open to the side patio, offering access to the hot tub, stunning mountain views, and lush gardens.

Additionally, a convenient half bathroom is situated just outside the primary bedroom.

Upstairs, discover two inviting bedrooms sharing a full bath with a tub/shower combination. One bedroom boasts a comfortable King bed, while the other offers a cozy Queen size bed. Both rooms feature additional play space for children or sleeping options within the finished alcove, detailed in the listing photos.

Embrace the convenience of a dedicated workspace crafted at the top of the landing on the second floor. Complete with a spacious desk, ample lighting, outlets, and picturesque mountain views, it offers the perfect setting for productive remote work.

The finished basement provides a quiet retreat, complete with a queen pullout, kitchenette, board games, and a tournament-quality foosball table. Stay active in the fully equipped gym featuring dumbbells, a power rack, bike, elliptical, treadmill. There is also a full bathroom with a shower located in the basement for your convenience.

The outdoor space not only features a heated pool and hot tub, but boasts a seating area under a covered pavilion with wood burning outdoor fire place. For nights when you don't want to build a fire, gather around the gas powered fire pit to relax. Dinner can be prepared in the outdoor kitchen and enjoyed on the covered deor poolside patio under the stars.

The extensive landscaping, tended by expert gardeners, creates an unparalleled ambiance for nature lovers and artists alike.
Enjoy the serenity of nature with 40 acres of wooded trails, a pond, meadow, and a year-round stream. Take in breathtaking mountain views on two sides of the property, with total privacy and the soothing sound of horses nearby.

Explore the enchanting pond, just a short walk from the home, featuring an enclosed gazebo, picnic tables, and a cleared meadow surrounded by majestic pines.

The outdoor space not only features a heated pool and hot tub, but boasts a seating area under a covered pavilion with wood burning outdoor fire place. For nights when you don't want to build a fire, gather around the gas powered fire pit to relax. Dinner can be prepared in the outdoor kitchen and enjoyed on the covered deor poolside patio under the stars.

Beyond being centrally located at the base of Greylock Mtn, this home is within 20- 30 minutes of many Berkshire hiking and water attractions, golf, Tanglewood, skiing, major art museums, dining, etc, activities for all interests. Ideal for a destination vacation, friend or family gathering, celebration, or relaxing.

Attractions close by include:
Pontoosuc Lake; 6 min
Ramblewild Adventure Park; 6 min
Mount Greylock; 7 miles, entrance 1 mile from home
Jiminy Peak Ski Resort; 9 min
Balance Rock; 9 min
Ioka Farms; 10 min
Wanbeeka Golf Links; 12 min
Rail Trail; 13 min
Onota Lake; 14min
Clark Art Institute; 20 min
Mass Moca; 25 min
Tanglewood; 30 min
Pittsfield Shopping / Downtown; 5-10 min

Having a car will greatly enhance your ability to explore the Berkshires effectively. Winter guests will need 4wd/Awd to access the property, but not studded snow tires. The driveway is long and rather steep.

LOCATION: Lanesborough is a quiet, rural community. There are horses next door, visible from the home.

PETS: A dog may be allowed with owner approval. Reach out with info about your pet prior to booking. A $100 pet fee will be incurred upon pet approval and booking. No multiples.

PARKING: Free parking on premises.

POOL: The pool is open seasonally fromMay through October, with exact opening and closing dates determined by weather conditions.

-FromJune 1st through Labor Day, the pool isheated to a comfortable 82°F at no additional cost. Guests who wish to maintain a higher temperature may do so for an additional fee, please reach out to us directly.

-Pool heating may also be available inMay and after Labor Dayfor anadditional charge of $150 per day.
To ensure the pool is ready upon your arrival, we kindly ask that you notify usin advanceif you plan to have the pool heated.

-If you wish to heat the pool above the standard 82°F provided between June 1 and Labor Day, an additional fee will apply. Please contact us in advance to confirm pricing and arrange for the higher temperature setting.

- There are 2 doors off the kitchen that will allow you access to the backyard pool. The doors have an alarm for safety, and must remain closed after the guest passes through to the pool. There is a fence around the pool area, but there is no fence or gate between the kitchen doors and the pool - guests will need to monitor small children at all times for safety.

*It is a 7-10 minute walk from the home, to the pond / pavilion area.

*Weekly discounts are available!

EVENTS: Small events may be accommodated on a case-by-case basis and may require additional fees beyond the nightly rental rate. All events must receive prior approval from the owner, and any vendors involved must have the appropriate permits.

Wifi Speed:
Download speed: 480 Mg/sec
Upload speed: 35 Mg/sec
Latency: 12 millisec

PLEASE NOTE: This property holds a special place in the hearts of its owners, who have dedicated time and effort to its renovations. While they cherish their time spent here, they warmly invite guests to treat the home with the same care and respect as they would their own. You are welcomed to embrace and fully enjoy the beauty of their home during your stay. For any inquiries or clarifications, please don't hesitate to reach out before booking.

**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

- "What a wonderful stay in the Berkshires! My wife and I loved the area so much. But the home, the beautiful pool and backyard, and the four legged neighbors made it difficult to venture out some days. The property provides privacy and plenty of activities (indoor and out). The home is warm and inviting with every amenity you could need: think country living at its finest, but with a modern flare. We look forward to visiting again for another romantic escape or perhaps a larger gathering of family and friends (easily could have accommodated another 3 couples or a couple families). Ruminating on the rocking chairs, listening to the birds and distant neighing… it’s simply perfect for any occasion. The home is centrally located between Lee/Lenox/Great Barrington and Williamstown/N. Adams. There are plenty of nearby shops and restaurants as well as hiking and picturesque mountain drives. We look forward to visiting again next year for another dose of exploration and r&r! Best, Megan and Bryan May 2024"

Wake up to spectacular sunrise lake views from the deck or while soaking in the hot tub. Close to all the year round activities in the Berkshires. A short drive to tanglewood, Norman Rockwell museum, Jacob’s Pillow, Mass Moca, Jiminy Peak Ski Resort, and Bosquet Ski Resort. You can hike, snow shoe, cross country ski, mountain bike and snow mobile at the numerous local state parks. Fish off and launch your paddle boat or kayak from your personal dock. You can even take a short walk down the street to the town sandy beach. The house comes with all the amenities and a fully loaded kitchen. A grill on the deck can be utilized year round. Cozy up to the outdoor fire pit while you lounge on the outdoor furniture. The yard is fenced in and pet friendly

- "Beautiful home for extended family vacation. Fishing, kayak and paddle board fun outdoors, plenty inside when its raining." - "The place was great, sitting on a lake in a quiet neighborhood with plenty to do nearby. The host was quick with communication, not that there was anything we had to bother him with. Highly recommend!" - "We had such a lovely time! The house was perfect for our two small families. We watched movies in the big living room, cooked a bunch in the extremely clean kitchen, and had a blast playing in the snow in the yard. Hope to return next year!"

Located in Lanesborough, guests love this Cozy Cottage aka “Polly’s Place” for its warmth, central location and accessibility to outdoor fun. Close to hiking, biking, skiing, fishing, lake activities, cultural venues and more. You can use it as a home base for exploring all of what the Berkshires have to offer or simply enjoy the quiet. The backyard is vast green park like setting to allow the kids to play ball or enjoy roasting marshmallows on the firepit. Retreat to the picnic table for outdoor dining.

The space
Our family home for over 70 years is a 1946 Classic New England Cape Cod. It sits on close to 2 acres at the crest of a hill with beautiful mountain views and sunsets as well as an enjoyable predominant breeze. There are four bedrooms, three upstairs and one on the ground level, an enclosed porch and sunken sunroom (with fireplace) looking out over the property. You may even spot a little wildlife! The home sleeps five comfortably and can sleep six if need be. The sunroom is a favorite for snuggling up with a book, sipping a cup of tea or a glass of wine or simply visiting with friends and family. There are smart T.V.s and game boards as well as a quiet office space. There is a highspeed multiport charger for multiple devices as well as two Bose speakers equipped with blue tooth for your listening pleasure.

Many outside and cultural adventures await to which we are centrally located. To name a few:

Jiminy Peak Mountain Resort, Hancock 7.6 miles
Bousquet Mountain Ski Area, Pittsfield 9.7 miles
Clark Art Institute, Williamstown 15 miles
Williams College, Williamstown 15 miles
Hancock Shaker Village 11miles
Pontoosuc Lake 2.7 miles
Tanglewood, Lenox 14 miles
Mass Moca, North Adams 15 miles
Visitor’s Center at Mt. Greylock, Lanesborough 3.5 miles
Ramblewild and Jiminy Peak Mountain Adventures, Lanesborough and Hancock 5.5 miles
Elle Day Spa, Lanesborough .8 miles
Ashuwillticook Rail Trail, Lanesborough 1mile
Norman Rockwell Museum, Stockbridge 20miles

Guest access
Polly’s Place is in a quiet residential neighborhood at the top of the hill with driveway parking. You will gain entry to the house through a lockbox located along side of the entryway door. The instructions to the lock box and the directions to the property with be provided prior to your arrival. A car will be needed to get around.

Other things to note
The kitchen is well equipped and well stocked for preparing meals.

You can harvest your own asparagus from our asparagus bed should you visit throughout the month of May and perhaps into early June. There is nothing better than fresh grilled asparagus!

There are multiple farms in the area from which to purchase locally sourced food.

This home is where Mikaela Shiffrin, Olympic and World Alpine Ski Champion, finds as a favorite respite after her busy ski racing season when coming home to the Berkshires to join family. She has been known to enjoy a family day of skiing locally and can be seen making " a few good turns" far from the hectic pace of the World Cup ski racing circuit.

Hosted by Annie and Patrick, avid skiers and former ski racers, we hope you will love the Berkshires as much as we do!

- "All in all, the stay was just fine. The property has a lot of idiosyncrasies, but the owners do everything they can to help you manage through them. Very clean and well appointed. " - "Really cute property with a spacious backyard, tho sadly we didn't stay long enough to take advantage of it. Close enough to walk to a nice diner for breakfast too! " - "The house is charming. We had a wonderful time cooking, playing games, even had an outdoor fire one night. We’ll stocked kitchen! Beds were comfortable!! Hosts were super friendly and responsive!!"

Hinterland Hall was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay.

When entering Hinterland Hall, the ground-level sanctuary is flooded with natural light from its nine twenty-foot tracery windows, two of which feature original stained glass from 1851. The sanctuary's expansive floor plan includes its original reclaimed wide plank pine flooring with rebuilt pine pews. The thirty-seven-foot cathedral ceilings feature their original shiplap finish.

Impossible to miss, the historic & rare hand-pumped organ was crafted in 1862 by the famed organ maker William Johnson of Westfield. It is number 134 of 860 ever made by Johnson and operates today as one of the oldest-working hand-pumped organs in the United States.

Many of these old organs have been burned in church fires, replaced by later models, electrified, or otherwise altered, but this one remains in its original condition and was professionally restored after our purchase. The sanctuary boasts impeccable acoustics.

Elements of the original gold foiled altarpiece remain surrounded by a cozy living area complete with an HD film projector and contemporary furnishings. Have a sip of whisky from the antique brass bar cart while making your way upstairs to the luxurious ensuite.

Follow the copper spiral staircase to an original early 19th-century full-length Louis Phillipe mercury glass mirror adjacent to a kitchenette, complete with a refrigerator, all-in-one compact oven, a pour-over Chemex coffee station, and selections of specialty snacks from Regalis Foods. Pop some Black Truffle Popcorn and curl up on a sheepskin for the perfect movie night.

Surrounded by glass, climb the steps inside the fully-encased native bluestone washroom. Take refuge in our luxurious concrete soaking tub for two or enjoy an open rain shower from the free-floating hammered brass shower head. Get wrapped up in our signature robes, curl into bed with hand-block-printed natural linens, and relax atop the live-edge pine frame. You’ll also find a large pullout drawer, perfect for storing clothing or a full suitcase.

Back downstairs, walk through the altar door to find yourself basking in pastoral views from the stone patio.

When outside, look up at the original bronze bell atop the bell tower. It was built in 1891 by Meneely & Co. Bell Company from West Troy, NY, and hoisted into position by horse carriage. Original marble stone platforms for unloading passenger carriages remain on the grounds today.

Hinterland Hall is nestled at the foothills of Mt. Greylock state reservation and is minutes away from Jiminy Peak, the tallest ski mountain in Massachusetts. Also nearby are Mass MoCA and The Clark, two must-visit world-class art institutions. For music lovers, Tanglewood is a short drive south in neighboring Lenox.

When entering Hinterland Hall, the ground-level sanctuary is flooded with natural light from its nine twenty-foot tracery windows, two of which feature original stained glass from 1851. The sanctuary's expansive floor plan includes its original reclaimed wide plank pine flooring with rebuilt pine pews. The thirty-seven-foot cathedral ceilings feature their original shiplap finish.

Impossible to miss, the historic & rare hand-pumped organ was crafted in 1862 by the famed organ maker William Johnson of Westfield. It is number 134 of 860 ever made by Johnson and operates today as one of the oldest-working hand-pumped organs in the United States.

Many of these old organs have been burned in church fires, replaced by later models, electrified, or otherwise altered, but this one remains in its original condition and was professionally restored after our purchase. The sanctuary boasts impeccable acoustics.

Elements of the original gold foiled altarpiece remain surrounded by a cozy living area complete with an HD film projector and contemporary furnishings. Have a sip of whisky from the antique brass bar cart while making your way upstairs to the luxurious ensuite.

Follow the copper spiral staircase to an original early 19th-century full-length Louis Phillipe mercury glass mirror adjacent to a fully stocked kitchenette, complete with a refrigerator, all-in-one compact oven, a pour-over Chemex coffee station, and selections of specialty snacks from Regalis Foods. Pop some Black Truffle Popcorn and curl up on a sheepskin for the perfect movie night.

Surrounded by glass, climb the steps inside the fully-encased native bluestone washroom. Take refuge in our luxurious concrete soaking tub for two or enjoy an open rain shower from the free-floating hammered brass shower head. Get wrapped up in our signature robes, curl into bed with hand-block-printed natural linens, and relax atop the live-edge pine frame. You’ll also find a large pullout drawer, perfect for storing clothing or a full suitcase.

Back downstairs, walk through the altar door to find yourself basking in pastoral views from the stone patio alongside a hand-forged fire pit for the perfect s'mores.

When outside, look up at the original bronze bell atop the bell tower. It was built in 1891 by Meneely & Co. Bell Company from West Troy, NY, and hoisted into position by horse carriage. Original marble stone platforms for unloading passenger carriages remain on the grounds today.

Hinterland Hall is nestled at the foothills of Mt. Greylock state reservation and is minutes away from Jiminy Peak, the tallest ski mountain in Massachusetts. Also nearby are Mass MoCA and The Clark, two must-visit world-class art institutions. For music lovers, Tanglewood is a short drive south in neighboring Lenox.

Please inquire for weddings & events
Follow us at @hinterlandhall

- "The owners have done a spectacular job of renovating this historic landmark. Being church musicians, we booked the church to celebrate our 25th anniversary. Jane was always a text away if we had any questions from booking to the actual stay. The pictures online are accurate to what you will find in real life. The free popcorn and whiskey were nice touches. Will definitely stay again." - "What an outstanding place to stay. The listing was exactly as advertised, and the church was so clean and comfortable. Communicating with the owners was very easy through the app. They got back to me quickly. The linens smelled great! Everything was provided. I recommend Hinterland Hall very highly! One of the best experiences I’ve had with any rental property. Can’t wait to come back! "

A masterpiece of contemporary design, this new custom-built home is a harmonious blend of modern luxury and nature’s splendor, nestled amidst the rolling hills of Lanesborough, Massachusetts. A sanctuary of sophistication, this exceptional residence is adorned with exquisite décor and arts and crafts by award-winning American artisans, offering an unparalleled living experience in one of Massachusetts’ most picturesque and culturally rich locales.

Step inside, and you are immediately captivated by the breathtaking open floor plan, where the kitchen, living, and dining areas flow seamlessly beneath soaring cathedral ceilings. Walls of glass invite the outdoors in, flooding the space with natural light and framing panoramic views of the Mount Greylock Reservation—a tableau of grandeur and serenity.

At the heart of this magnificent home lies a gourmet kitchen, an epicurean’s delight, equipped with top-tier appliances, bespoke cabinetry, and a spacious 6' x 7' island, perfect for casual gatherings or culinary artistry with a view. For those who delight in culinary artistry, this home offers an unparalleled opportunity to craft exquisite farm-to-table meals. Use an array of fresh, organic herbs and spices from our own carefully curated selection, infusing your dishes with vibrant, homegrown flavors. Just five minutes away, Red Shirt Farm provides a bounty of organic vegetables, allowing you to create seasonal, nutrient-rich feasts that celebrate the very essence of fresh, local ingredients. Here, the kitchen becomes more than a space—it is a sanctuary of creativity, nourishment, and connection to the land.The adjacent living area exudes warmth and refinement, anchored by a sleek gas fireplace—an invitation to relax in its glow as you gaze upon the majestic mountain vista. In the elegant dining space, 8-10 guests can revel in sun-drenched ambiance, setting the stage for unforgettable meals and spirited conversation.

The home’s four well-appointed bedrooms offer peaceful retreats, with the primary suite serving as a true oasis of indulgence. Featuring a private gas fireplace, a luxurious en-suite bath, and a generous walk-in closet, this haven of relaxation is crowned by a spa-like bathroom, complete with heated floors, a freestanding soaking tub, and an expansive tiled shower—a private escape into serenity. With two additional full baths and two half baths, comfort and convenience abound.

Step outside to the expansive 12' x 24' deck, where morning coffee or evening cocktails become a ritual in tranquility, with uninterrupted views of rolling pastures and misty mountains. Below, a sprawling 1,000-square-foot patio awaits, complete with a built-in gas grill, dining table, and plush lounge seating—the perfect setting for al fresco gatherings. As dusk settles, gather around the fire pit, where laughter and conversation mingle beneath a canopy of stars.

The estate’s meticulously landscaped grounds are a testament to careful craftsmanship, with vibrant flower beds and lush greenery accentuating its curb appeal. A graceful circular driveway provides ample parking, while a three-car garage ensures seamless storage for vehicles and recreational gear.

Beyond its sheer beauty, this home offers a lifestyle infused with wellness and recreation. Engage in friendly lawn games of badminton and cornhole, or embrace the cutting-edge bio-hacking technology designed for optimal health. From the German-engineered Carol stationary bike with HIIT AI assistance to an infrared personal sauna, a Joovv red light therapy panel, a workout trampoline, TB12 and TRX bands, and free weights, every detail has been curated to support vitality and well-being.

Located in the heart of the Berkshires, this residence is a gateway to world-class cultural and outdoor pursuits. Ski the slopes of Jiminy Peak, explore the treetop adventures of Ramblewild, hike the legendary trails of Mount Greylock, or immerse yourself in art and music at the Clark Museum, Mass MoCA, and Tanglewood. Indulge in the magic of Shakespeare & Company, Jacob's Pillow, and experience the vibrant cultural scene that makes the Berkshires an unparalleled destination. Many nearby golf courses, and Baker's Golf driving range and mini golf recreation area next to Krispy Kone for great Ice cream and lunch

This extraordinary home is more than a residence—it is a lifestyle, where luxury, nature, and culture converge in perfect harmony.

- "The house was absolutely amazing. So comfortable and clean and beautiful. Would definitely stay again!" - "We loved Bob and Irene's house! We had 4 adult couples and an infant staying. It was so nice every couple had their own room and bathroom! We spent the whole weekend with all the windows and sliding door open, it was so nice to be in nature and enjoy the property. We utilized the big open kitchen and dining area with lots of food and games. The local area had tons of options for food, beverages and ice cream!We will definitely look to stay here again if we are in the area in the future."

Fully funished charming openspace house with kitchen dining and living areas,
modern wood stove , contemporary master bedroom, additional bedroom with trundel beds, wrap around deck, large yard areas and more.

This location is private and located on one of the lovliest roads around. It is very well situated to numerous nearby regional attractions. In particular, Ski Resorts and expansive Hiking and Recreaction areas, Museums, Theater, Music and other arts. It is spectacular during fall foliage time and very fun during winter, spring and summer.

Child Friendly • Laundry • Security/Safety